life coach for women, midlife, empty nest, coach, next act, coaching for women

Flipping Houses in Midlife: Lisa’s Story


Between Lisa’s small business and her alimony, she was able to support herself. But with only one year of alimony payments remaining, she had to find a way to supplement her income. She used her realtor and design experience to buy and renovate her first house and got the bug.


Tell us a little about your background.

I grew up in Overland Park, Kansas (a suburb of Kansas City), with my four siblings (I’m in the middle) and my parents, all of who still live in Kansas City. My dad is from Poland and my mom is from Mexico. I am the first generation American on both sides of my family.

As a child (the blonde)

As the proud mom of two sons in college (my oldest is graduating in a few weeks), I live in Dallas, TX. My boyfriend and I live in different cities but spend one week at his home in Kansas City and the following week in Dallas. Southwest Airlines loves us!

After graduating from college, I sold radio time for a talk radio station, was a special events coordinator for Macy’s in the Midwest, and then was the Licensing Director for Universal Licensing (a division of Universal Press Syndicate). I worked with Gary Larson (The Far Side), Cathy Guisewite (Cathy) and other cartoonists to secure licensing deals.

After I quit Universal, I became a professional organizer and started my company Everything’s Organized. It eventually evolved into another business called Home Office Life. I’ve written five books about working from home. They were published by major publishers, by smaller houses, and self-published.

When did you start to think about making a change?

In my business,  I was working with clients to help them design home offices and was giving seminars around the country. I was also a spokesperson for various campaigns for Office Depot, Avery, Day Runner and Fuji. I had been a work-from-home mom for years and while my business was profitable, my (then) husband and I didn’t rely on my income to pay bills.

After my divorce and a year before my alimony was set to run out, I knew I had to focus on creating a business that would allow me to support myself. One option was to find a full-time job but, after being an entrepreneur for so many years, I knew I couldn’t work for someone else.

What is your next act?

I buy houses to either flip or rent. I started my company, Imagine Property Group, in 2013, at the age of 52. Currently, I own seven single-family homes in and around Dallas, TX. Prior to my divorce, I earned a degree in Interior Design that has helped me with my house rehab projects. I also invest in multi-family properties. My success as a real estate investor allows me the freedom to write, another one of my passions.

As the project manager for each of the homes I buy, I schedule the subcontractors and track every aspect of the project. I buy homes with the purpose of setting them up as rentals, but on a few occasions, after seeing the results, I’ll put the house on the market. Tenants are hard on rentals.

I love taking a neglected property (the worse shape it’s in, the better) and turn it into a beautiful home I am proud to rent or sell to others. When we’re working on a home, the neighbors often come by to see what changes we are making and are happy to see the results. An updated or completely renovated home increases their property values and adds to the look of the neighborhood. Seeing a dramatic transformation encourages me to find more houses to rehab.

Kitchen — Before

Kitchen — After

Why did you choose this next act?  

I fell into this next act by accident. While compiling paperwork for my divorce, I called a guy with whom my family had invested; he told me about a real estate investment group he was in and I attended a meeting. After learning more about buying and rehabbing houses, I was hooked. I felt this was the perfect way to merge my design skills with a growing industry. As a former special events coordinator, I enjoy planning projects and seeing them through to completion.

Another option I considered was being a translator. I am fluent in Spanish and thought that may be a career path for me. I decided against it because my sons were still in school and I would have needed to take classes and train to be an interpreter. After juggling design school and my family, I wasn’t ready to enroll in classes again.


How hard was it to take the plunge?

Without the real estate investment group and the various members I met, I don’t think I would have had as much confidence to invest money right away. Mentally, my first house was the toughest to buy. It needed a lot of work: flooring, countertops, foundation, painting, new bathrooms, fixtures, etc. After I bought and rehabbed that house, I was ready to buy more.

Here’s the first house I flipped:

How supportive were your family and friends?

My boyfriend, Perry, and my sons have been the most supportive of my business. Perry encouraged me to buy my first house. Actually, his exact words were, “If you don’t buy it, I will.” I knew he wouldn’t, but it was what I needed to hear to move forward.

My family probably thought I was insane when I showed them the “before” photos, but when they saw the “after” photos, they understood what I was doing. My sons occasionally help me in the summer with various projects. I want to teach them to invest in real estate. I wish I had known how to do that when I was their age!

With my sons

What challenges did you encounter?

Finding the right subcontractors was challenging and staying on budget wasn’t easy. By the third house, I had a good system for purchasing materials (the materials aren’t expensive…it’s the labor) and had compiled a good crew to help me update or completely rehab houses on time and within my budget. With the exception of two subcontractors, I still work with the same subcontractors.


Were there times when you thought about giving up?  

I’ve never thought about giving up because I love what I do. The construction and housing industry has changed so finding houses at a reasonable price is challenging. I haven’t flipped a house in over a year, but plan to do so again when I can purchase properties at a better price.

In the meantime, I manage my properties on my own. My tenants treat the houses well and when I put a house on the market to rent, I find qualified tenants within a week. Whenever someone asks me what I do, they often reply, “I’d love to do that!” Knowing that I am building a business I enjoy that allows me to support myself encourages me to continue following my career path. Also, not having a boss is a strong motivator!

My home office is my screened-in porch. I also work from my car and Starbucks.

What did you learn about yourself through this process?

I learned that it’s possible to do something you enjoy and make a very good living. I’ve also learned you’re never too old to learn new skills. I used to call my handyman to make simple repairs, but I’m able to fix a few things by myself. I manage an all-male crew and they respect me. I pay quickly and when I have a repair request, I can get someone to take care of it within a day or two.


Looking back, is there anything you’d have done differently?

I would have bought more houses when prices were low! It’s too bad I didn’t have a crystal ball to be able to predict the crazy housing market. But my focus moving forward is on purchasing foreclosures. By renovating foreclosed and neglected homes, I can add something positive to a neighborhood and grow my business.

Selecting flooring for a project

What advice do you have for women seeking reinvention in midlife?

I didn’t believe the adage, “Do what you love and the money will come,” because I enjoyed my home office business, but I wasn’t making enough money to support myself. But, if you dig deep to find a passion, you can be financially successful and fulfilled.

Age should not be a barrier or excuse to avoid pursuing a new career path. When my sons were younger, one asked me what I wanted to be when I grow up. I think I’m still figuring that out! The possibilities are endless.

Canyoning in Costa Rica

What advice do you have for those interested in flipping houses? What resources do you recommend?

Be willing to take risks. Decide how much money you are willing to invest in a house. Read online what you can about being a landlord, rehabbing properties, and selling houses. I am also a realtor so I can save money when I buy and sell my homes. offers valuable real estate insight.

The investment group I joined is called Lifestyles Unlimited (they are based in Texas). Check for similar groups in your area.

Beware of online courses that promise “the secrets” to flipping and owning real estate. They can be expensive and offer nothing more than what you would learn through a realtor who specializes in working with investors, which is someone you will want to find.

Before I had any interest in real estate investing, I read Rich Dad Poor Dad: What the Rich Teach Their Kids About Money That the Poor and Middle Class Do Not! and then put it aside. Robert T. Kiyosaki’s book is a good introduction to flipping houses, but times and regulations have changed. The experts I follow are my fellow investors. One friend owns 18 single family houses and an 80-unit apartment complex. Another owns five 300-unit multifamily properties and is in the process of flipping two of them. They are always available for advice.

As far as TV shows, I have watched Flip or Flop a few times and it is a fairly true representation of the work that goes into flipping a house. They hire a contractor to do the work vs. other shows that encourage the investor to do the work on his or her own. The goal is to renovate a house quickly to be able to get it on the market, yet the work needs to be high quality. Being able to buy houses at an auction appears much easier on that show than it truly is. There are more investors now, searching and bidding on homes, than before. I buy my homes through wholesalers and banks. During one episode of Flip or Flop, I was on the phone with my sister as the couple toured the home. I could immediately see a few of the repairs they needed to make and told my sister before the contractor mentioned them. I’ve toured so many homes in need of repair that I no longer notice what horrible shape they’re in! All I see is the end result. My sister and her daughter are huge fans of Fixer Upper so I’ve started watching that show and Joanna’s design choices.

Transforming wasted space into useful space in a bathroom:

What’s next for you?

I’m going to look for more properties to flip and rent, and explore other real estate investment options (office/warehouse spaces).

Along with real estate investing, I am focusing on improving my writing skills and compiling a wish list of the publications and websites in which I would like to be published. Being a real estate investor provides me the freedom to pursue writing and other passions I know I’ll continue to discover.


Contact Lisa Kanarek at


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8 Responses

  1. I love stories like this! I think it is so inspiring when women in their 50’s make a big transition like this and find success. It just shows that it is never too late to find what you love and start doing it. Thanks for sharing!

  2. Your book “Working Naked” seems interesting. I wonder if it’s in amazon for purchase? I am asking because I would like to try working at home and maybe do a home office. So I would really love to get a hold of your book. Thanks for sharing

    1. Yes, Working Naked is available as an ebook on Amazon. It provides overall tips for setting up a home office and working from home. For a more detailed guide to working from home, I recommend my book Organize Your Home Office For Success (also an e-book). It also includes before and after photos of home offices. Good luck!

  3. Mindy

    I don’t know what Lisa wants to be when she grows up, but when I grow up, I want to be Lisa! I love stories like this. They’re so motivating. Thanks for sharing it!

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